Training Videos - Trans (87,364)

Anal training!

xHamster 2 weeks ago

Hard Sissy Training and Sissygasm Compilation

Hard Sissy Training and Sissygasm Compilation

xHamster 3 weeks ago

Sophia Loreen Party on Dec 23, 2025 - Part 2

56% 4K 2:00 / 33:49

Sophia Loreen Party on Dec 23, 2025 - Part 2

Flirt4Free 2 months ago

”Goddess Kyaa & River Enza in Gape Training 3”

”Goddess Kyaa & River Enza in Gape Training 3”

Faptor 9 months ago

becomingfemme - jazmin household sissy maid learns her place

becomingfemme - jazmin household sissy maid learns her place

TransDoe 2 years ago

8. bi-slave-gang-bang part 3 - anal explosion and mega cumshot

8. bi-slave-gang-bang part 3 - anal explosion and mega cumshot

FapHouse 4 years ago

Sex Training

ShemaleSin 6 days ago

Femboy Gape Compilation #2 fart-gapes

Femboy Gape Compilation #2 fart-gapes

xHamster 1 month ago

Day 2 Tease and Denial

HD 0:39 / 11:23

Day 2 Tease and Denial

FapHouse 3 months ago

Anal masturbation in women's clothes with toys and a little zucchini,anal orgasm sissy

Anal masturbation in women's clothes with toys and a little zucchini,anal orgasm sissy

xHamster 5 months ago

Ladyboy Jizzing hump female dominance domina, Pulverize cunt Sissy

Ladyboy Jizzing hump female dominance domina, Pulverize cunt Sissy

TrannyGem 1 year ago

Sex Training

FapHouse 3 weeks ago

In Sissy Clothes, This Is How You'll Soon Look

In Sissy Clothes, This Is How You'll Soon Look

FapHouse 2 weeks ago

Sasha de Sade is trained by Mistress

Sasha de Sade is trained by Mistress

aShemaleTube 9 years ago

Tied up Shemale Rides Big Dildo and Sissygasm

Tied up Shemale Rides Big Dildo and Sissygasm

xHamster 5 months ago

Kitty training her ass

Kitty training her ass

Tranny.one 10 months ago

Luke Hardy & Cristian Ford Private Show

48% HD 2:00 / 18:14

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

Sissy Kate learns how to use the anal fucking machine with Lisa

Sissy Kate learns how to use the anal fucking machine with Lisa

xHamster 2 years ago

Lanna & Nefertiti Private Show

HD 2:00 / 30:20

Lanna & Nefertiti Private Show

Flirt4Free 2 years ago

My sissyboy gets three ruined orgasms in a row. No real orgasm for boys in lace panties! Femdom and feminization

My sissyboy gets three ruined orgasms in a row. No real orgasm for boys in lace panties! Femdom and feminization

xHamster 1 year ago

Glam Slut Milking Training 2

HD 0:39 / 20:26

Glam Slut Milking Training 2

FapHouse 1 month ago

FULL MOVIE Lena Vesper Railed By Hankeys Seahorse Bang Machine

FULL MOVIE Lena Vesper Railed By Hankeys Seahorse Bang Machine

SortPorn 3 months ago

A Sissy for the Cheer Team

A Sissy for the Cheer Team

ShemaleSin 1 month ago

Lick daddy's dirty feet, suck a big dick!

Lick daddy's dirty feet, suck a big dick!

xHamster 3 years ago

Wild Sabrina Private Show

Wild Sabrina Private Show

Flirt4Free 4 years ago

AB085 Lustful Abby Kitty be Master's sissy slave -chastity 堕落成为主人的淫荡人妖锁奴母狗

AB085 Lustful Abby Kitty be Master's sissy slave -chastity 堕落成为主人的淫荡人妖锁奴母狗

aShemaleTube 2 years ago

Making You Into My Own Little Sissy Fuck Toy

62% HD 0:39 / 13:48

Making You Into My Own Little Sissy Fuck Toy

FapHouse 11 months ago

Instructions From the Trainer No 11 Daily Exposure Walks

HD 0:39 / 10:20

Instructions From the Trainer No 11 Daily Exposure Walks

FapHouse 6 days ago

Women Pub Vignette five: A Sissy Feminization Series

Women Pub Vignette five: A Sissy Feminization Series

TrannyGem 5 years ago

Sissy crossdresser masturbating cum eating playing cock flapping balls tucked Femboy masturbation Sissygasm Asspussy

Sissy crossdresser masturbating cum eating playing cock flapping balls tucked Femboy masturbation Sissygasm Asspussy

xHamster 3 years ago

He fucks me like a bitch... I love being trained by Master - @Sasha_de_Sade & @AxelReigns

He fucks me like a bitch... I love being trained by Master - @Sasha_de_Sade & @AxelReigns

aShemaleTube 1 year ago

Ryley Rails Edging JOI

Ryley Rails Edging JOI

xHamster 3 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 4 days ago

Redhead beauty in chastity trains her sissy to use her mouth and ass

Redhead beauty in chastity trains her sissy to use her mouth and ass

TrannyMovs 5 days ago

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 9 months ago

Gorgeous transsexual Venus Lux fiercely bangs a hot young guy

Gorgeous transsexual Venus Lux fiercely bangs a hot young guy

Tranny.one 8 years ago

Jerking in the afternoon. Do you like my wooly gams? And cooter? And bunghole?

Jerking in the afternoon. Do you like my wooly gams? And cooter? And bunghole?

TrannyGem 3 years ago

my husband turns his pathetic cock into a pretty pussy

my husband turns his pathetic cock into a pretty pussy

xHamster 2 years ago

Leela's Blowjob Experience

Leela's Blowjob Experience

xHamster 2 years ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 3 days ago

Boot-licking Foot TS Slave Ariel Demure - Brittany Andrews

64% HD 0:10 / 18:50

Boot-licking Foot TS Slave Ariel Demure - Brittany Andrews

LoyalFans 2 years ago

Cougar was nosey What the depth of my Bootie Tastes Like, so she Screwed me with a Faux-Cock and Munched it

Cougar was nosey What the depth of my Bootie Tastes Like, so she Screwed me with a Faux-Cock and Munched it

TrannyGem 1 year ago

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

429Men 1 month ago

Restraint training in Onepeace

Restraint training in Onepeace

xHamster 3 years ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 1 week ago

Cute Blonde Sissy Lactating her Tits and Spanking her Big Boobs with Black Cock

Cute Blonde Sissy Lactating her Tits and Spanking her Big Boobs with Black Cock

xHamster 5 days ago

Feminized ladyboy gets vulva plowed

Feminized ladyboy gets vulva plowed

TransTube.tv 1 year ago

Anal Orgasm in Chastity

Anal Orgasm in Chastity

xHamster 1 week ago

TS French Maid Anal Training

TS French Maid Anal Training

aShemaleTube 5 years ago

Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!

Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!

xHamster 10 months ago

Ts Isabella sissy passions for his English Mistress

62% HD 1:01 / 24:03

Ts Isabella sissy passions for his English Mistress

FapHouse 3 years ago

Sissy Presenting New Dress and Small Walk Around Outdoor

Sissy Presenting New Dress and Small Walk Around Outdoor

xHamster 3 months ago

Crossdresser in High Heels Gets Anal Pussy Machine Fucked

Crossdresser in High Heels Gets Anal Pussy Machine Fucked

xHamster 7 months ago

Luke Hardy & Cristian Ford Private Show

62% 4K 2:00 / 21:06

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 month ago

Trainer's Training Session No. 92: Restrained Masturbation and Abandonment

Trainer's Training Session No. 92: Restrained Masturbation and Abandonment

FapHouse 2 weeks ago

sissy gal ass fucking trainer with penetrate machine big black cock fake-manstick

sissy gal ass fucking trainer with penetrate machine big black cock fake-manstick

TransTube.tv 1 year ago

Corporate Training 2 3D Futanari Animation

Corporate Training 2 3D Futanari Animation

Nuvid 1 year ago

Let’s cum jointly

Let’s cum jointly

ShemaleSin 4 years ago

Viky & Master Private Show

63% HD 2:00 / 25:32

Viky & Master Private Show

Flirt4Free 6 months ago

Humiliation for Sissy JOI Experience

Humiliation for Sissy JOI Experience

xHamster 4 months ago

Beauty Ebony Fucked in Pov

63% HD 2:00 / 11:50

Beauty Ebony Fucked in Pov

Flirt4Free 3 years ago

Trainer's Training Session No. 99: Outdoor Spread-leg Tackle with Exposed Cunt

63% HD 1:01 / 6:49

Trainer's Training Session No. 99: Outdoor Spread-leg Tackle with Exposed Cunt

FapHouse 1 week ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 4 days ago

My Hotwife Gameplay - Part 6 - the Book of Cuckolding

My Hotwife Gameplay - Part 6 - the Book of Cuckolding

xHamster 3 months ago

”Natalie Mars Helps Bestie Explore Assfucking Fantasies with Toys & Strap-On”

”Natalie Mars Helps Bestie Explore Assfucking Fantasies with Toys & Strap-On”

LesbianBliss 2 months ago

Sissy coming home from work

Sissy coming home from work

2BGay 7 months ago

Stunning moment from "90 pumps on inflatable long dildo all the way in extreme anal training for sissy sub slut"

Stunning moment from "90 pumps on inflatable long dildo all the way in extreme anal training for sissy sub slut"

xHamster 6 months ago

Making My Cock Explode

Making My Cock Explode

xHamster 4 months ago

Pegged Anal Whore Jasmine *FULL-HD*

66% HD 0:10 / 6:50

Pegged Anal Whore Jasmine *FULL-HD*

LoyalFans 2 weeks ago

Housewife Breeding By Super-fucking-hot She-creature Shooting Her Jizm Deep Inside My Wife Twat

Housewife Breeding By Super-fucking-hot She-creature Shooting Her Jizm Deep Inside My Wife Twat

TransTube.tv 1 year ago

Alexxa & Francesco Private Show

55% HD 2:00 / 4:56

Alexxa & Francesco Private Show

Flirt4Free 2 years ago

Playtime 69

xHamster 5 months ago

”TS anal fucks police cadet”

”TS anal fucks police cadet”

HQBang 2 years ago

Dumb femboy is getting trained

Dumb femboy is getting trained

xHamster 2 weeks ago

New huge Monstercock for greedy crossdresser anal pussy

New huge Monstercock for greedy crossdresser anal pussy

xHamster 3 weeks ago

Rubber slave anal training

Rubber slave anal training

xHamster 1 month ago

Sissy Maid Covered with Fake Cum and Breaks Her Fucking Machine Before Having a Sissygasm

Sissy Maid Covered with Fake Cum and Breaks Her Fucking Machine Before Having a Sissygasm

xHamster 1 year ago

Hijab Maid

FapHouse 1 year ago

Slut in transparent clothing ball gag and LED dog collar caught in public

Slut in transparent clothing ball gag and LED dog collar caught in public

xHamster 3 years ago

Screwing Faggot

Screwing Faggot

ShemaleSin 4 years ago

SpandexFemBoy - Long BBC Anal Ride Dildo Action Sissy

SpandexFemBoy - Long BBC Anal Ride Dildo Action Sissy

xHamster 2 months ago

Hubby becomes sissy bitch for wife

Hubby becomes sissy bitch for wife

Fapcat 2 months ago

Sissy Foot Fetish Job Interview Episode - Footjob And Oral-sex Training Chastity Doxy Jessica Bloom

Sissy Foot Fetish Job Interview Episode - Footjob And Oral-sex Training Chastity Doxy Jessica Bloom

ShemaleSin 1 year ago

Crossdresser Machine Fuck training

Crossdresser Machine Fuck training

xHamster 2 years ago

Brie Lovely Trains to Be a Slut

HD 0:39 / 31:25

Brie Lovely Trains to Be a Slut

FapHouse 2 months ago

Woman Fucks Her Husband By The Anus #047 Training Sissy Lesbian Dildo

Woman Fucks Her Husband By The Anus #047 Training Sissy Lesbian Dildo

xHamster 11 months ago

Ryley Rails Dominates You

Ryley Rails Dominates You

xHamster 4 months ago

Multiformity Itsol HFO training mindfuck

Multiformity Itsol HFO training mindfuck

FreePorn8 1 month ago

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 6

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 6

xHamster 1 month ago

Sophia Loreen Private Show

4K 2:00 / 21:43

Sophia Loreen Private Show

Flirt4Free 3 months ago

Your Dominant-Bitch Wishes Butt Worship. a sure way to Earn your Place!

Your Dominant-Bitch Wishes Butt Worship. a sure way to Earn your Place!

ShemaleSin 5 years ago

Muscle Trans

FapHouse 1 year ago

Beauties of anal delights part 2

Beauties of anal delights part 2

xHamster 1 year ago

Extreme Huge Man Nipples Titten-Sau Nipple Pain Slut FAG

Extreme Huge Man Nipples Titten-Sau Nipple Pain Slut FAG

xHamster 2 years ago

Brazilian tgirl slut training💋💘

Brazilian tgirl slut training💋💘

aShemaleTube 1 year ago

Briana & Deimon Private Show

61% HD 2:00 / 13:27

Briana & Deimon Private Show

Flirt4Free 1 year ago

BNWO Sissy Bride Gooning

BNWO Sissy Bride Gooning

xHamster 5 months ago

Mistress Baton’s Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

61% HD 1:01 / 24:06

Mistress Baton’s Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

FapHouse 2 months ago

Monica Farell Private Show

Monica Farell Private Show

Flirt4Free 1 year ago

TS Nadia Love titty fucking and sucking shaft of a black guy

TS Nadia Love titty fucking and sucking shaft of a black guy

Sheshaft 5 years ago

Domme Jardena in assfucking transgender sesh . Utter vid on my Onlyfans ( fasten in bio)

Domme Jardena in assfucking transgender sesh . Utter vid on my Onlyfans ( fasten in bio)

TrannyGem 2 years ago

Milking the first drops from my SISSY's PROSTATE

Milking the first drops from my SISSY's PROSTATE

xHamster 1 year ago

Another lesson with a pink strapon and a sissy slut in a sexy bodysuit

Another lesson with a pink strapon and a sissy slut in a sexy bodysuit

xHamster 1 year ago

Jules Trains Her Sub

58% 0:39 / 25:46

Jules Trains Her Sub

FapHouse 2 years ago

SEXY CLIMAX CUMSHOTS COMPILATION

SEXY CLIMAX CUMSHOTS COMPILATION

ShemaleSin 1 year ago

Sissy Riding Two Different Dildos

Sissy Riding Two Different Dildos

xHamster 1 year ago

Sophia Loreen Party on Apr 3, 2025 - Part 17

46% 4K 2:00 / 11:32

Sophia Loreen Party on Apr 3, 2025 - Part 17

Flirt4Free 10 months ago

Sissygasm in Underpants

Sissygasm in Underpants

GayCK 6 years ago

Sophia Loreen Private Show

55% 4K 2:00 / 6:34

Sophia Loreen Private Show

Flirt4Free 2 months ago

Stepmommy Turns Philip into Sissy Superslut Phillipa point of view Rollplay

Stepmommy Turns Philip into Sissy Superslut Phillipa point of view Rollplay

TransTube.tv 1 year ago

Double Stuffed Bimbo

Double Stuffed Bimbo

xHamster 9 months ago

Jessica Bloom Takes Fist And Foot Up Her Slutty Asshole Until She Cums Anal Fisting And Footing

Jessica Bloom Takes Fist And Foot Up Her Slutty Asshole Until She Cums Anal Fisting And Footing

xHamster 1 year ago

Strenuous SISSYGASM on phat BIG BLACK COCK fake-shaft!

Strenuous SISSYGASM on phat BIG BLACK COCK fake-shaft!

TransTube.tv 1 year ago

Trans Catgirl Screw Machine Sissy Training

Trans Catgirl Screw Machine Sissy Training

ShemaleSin 4 years ago

Saturday afternoon training

Saturday afternoon training

xHamster 9 months ago

ショッピングモールでロングディルドオナニー

ショッピングモールでロングディルドオナニー

TrannyGem 3 years ago

show bigcum - Part 3

HD 2:00 / 14:49

show bigcum - Part 3

Flirt4Free 1 year ago

Sissy in Fishnet Is Squirting While She Gets Deep Anal Fisted

50% HD 0:39 / 3:13

Sissy in Fishnet Is Squirting While She Gets Deep Anal Fisted

FapHouse 4 months ago

Sissy Bathroom Series - Crimson Satin and Mesh Ouvert Underwear Set

Sissy Bathroom Series - Crimson Satin and Mesh Ouvert Underwear Set

4Gay 3 weeks ago

TGIRLS XXX: White Chinaa's Massage Skills

TGIRLS XXX: White Chinaa's Massage Skills

xHamster 3 years ago

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